Amsacrine HCl
Amsacrine is an aminoacridine derivative with potential antineoplastic activity. Although its mechanism of action is incompletely defined, amsacrine may intercalate into DNA and inhibit topoisomerase II, resulting in DNA double-strand breaks, arrest of the S/G2 phase of the cell cycle, and cell death. This agent's cytotoxicity is maximal during the S phase of the cell cycle when topoisomerase levels are greatest. In addition, amsacrine may induce transcription of tumor promoter p53 protein and block p53 ubiquitination and proteasomal degradation, resulting in p53-dependent tumor cell apoptosis.
1: Jangir DK, Kundu S, Mehrotra R. Role of minor groove width and hydration pattern on amsacrine interaction with DNA. PLoS One. 2013 Jul 29;8(7):e69933. doi: 10.1371/journal.pone.0069933. Print 2013. PubMed PMID: 23922861; PubMed Central PMCID: PMC3726726.
2: Krejci M, Doubek M, Dusek J, Brychtova Y, Racil Z, Navratil M, Tomiska M, Horky O, Pospisilova S, Mayer J. Combination of fludarabine, amsacrine, and cytarabine followed by reduced-intensity conditioning and allogeneic hematopoietic stem cell transplantation in patients with high-risk acute myeloid leukemia. Ann Hematol. 2013 Jun 1. [Epub ahead of print] PubMed PMID: 23728608.
3: Schaich M, Parmentier S, Kramer M, Illmer T, Stölzel F, Röllig C, Thiede C, Hänel M, Schäfer-Eckart K, Aulitzky W, Einsele H, Ho AD, Serve H, Berdel WE, Mayer J, Schmitz N, Krause SW, Neubauer A, Baldus CD, Schetelig J, Bornhäuser M, Ehninger G. High-dose cytarabine consolidation with or without additional amsacrine and mitoxantrone in acute myeloid leukemia: results of the prospective randomized AML2003 trial. J Clin Oncol. 2013 Jun 10;31(17):2094-102. doi: 10.1200/JCO.2012.46.4743. Epub 2013 Apr 29. PubMed PMID: 23630210.
4: Fong CY, Grigoriadis G, Hocking J, Coutsouvelis J, Muirhead J, Campbell P, Paul E, Walker P, Avery S, Patil S, Spencer A, Schwarer A, Wei A. Fludarabine, cytarabine, granulocyte-colony stimulating factor and amsacrine: an effective salvage therapy option for acute myeloid leukemia at first relapse. Leuk Lymphoma. 2013 Feb;54(2):336-41. doi: 10.3109/10428194.2012.713479. Epub 2012 Sep 8. PubMed PMID: 22812445.
5: Jangir DK, Dey SK, Kundu S, Mehrotra R. Assessment of amsacrine binding with DNA using UV-visible, circular dichroism and Raman spectroscopic techniques. J Photochem Photobiol B. 2012 Sep 3;114:38-43. doi: 10.1016/j.jphotobiol.2012.05.005. Epub 2012 May 18. PubMed PMID: 22677564.
6: Ketron AC, Denny WA, Graves DE, Osheroff N. Amsacrine as a topoisomerase II poison: importance of drug-DNA interactions. Biochemistry. 2012 Feb 28;51(8):1730-9. doi: 10.1021/bi201159b. Epub 2012 Feb 10. PubMed PMID: 22304499; PubMed Central PMCID: PMC3289736.
7: Attia SM. Molecular cytogenetic evaluation of the mechanism of genotoxic potential of amsacrine and nocodazole in mouse bone marrow cells. J Appl Toxicol. 2013 Jun;33(6):426-33. doi: 10.1002/jat.1753. Epub 2011 Nov 11. PubMed PMID: 22081495.
8: Devi ML, Chandrasekhar KB, Surendranath KV, Rao BM, Narayana MB. A validated stability-indicating RP-HPLC assay method for Amsacrine and its related substances. J Chromatogr Sci. 2011 Aug;49(7):489-94. PubMed PMID: 21801478.
9: Wilhelm C, Neubauer A, Burchert A. Poor-risk cytogenetics may be associated with inferior outcome after fludarabine, cytarabine, and amsacrine reduced intensity conditioning in patients with high-risk acute myeloid leukemia. Leuk Lymphoma. 2011 Oct;52(10):2031-5. doi: 10.3109/10428194.2011.588760. Epub 2011 Jun 24. PubMed PMID: 21702642.
10: Zhang L, Guo Y, Wang J, Wang X, Han G, Ou W, Xu Y, Zhang X. Assisted sonodynamic damage of bovine serum albumin by metronidazole under ultrasonic irradiation combined with photosensitive antitumor drug-Amsacrine. J Photochem Photobiol B. 2010 Jan 21;98(1):61-8. doi: 10.1016/j.jphotobiol.2009.11.005. Epub 2009 Nov 22. PubMed PMID: 20006932.
2: Krejci M, Doubek M, Dusek J, Brychtova Y, Racil Z, Navratil M, Tomiska M, Horky O, Pospisilova S, Mayer J. Combination of fludarabine, amsacrine, and cytarabine followed by reduced-intensity conditioning and allogeneic hematopoietic stem cell transplantation in patients with high-risk acute myeloid leukemia. Ann Hematol. 2013 Jun 1. [Epub ahead of print] PubMed PMID: 23728608.
3: Schaich M, Parmentier S, Kramer M, Illmer T, Stölzel F, Röllig C, Thiede C, Hänel M, Schäfer-Eckart K, Aulitzky W, Einsele H, Ho AD, Serve H, Berdel WE, Mayer J, Schmitz N, Krause SW, Neubauer A, Baldus CD, Schetelig J, Bornhäuser M, Ehninger G. High-dose cytarabine consolidation with or without additional amsacrine and mitoxantrone in acute myeloid leukemia: results of the prospective randomized AML2003 trial. J Clin Oncol. 2013 Jun 10;31(17):2094-102. doi: 10.1200/JCO.2012.46.4743. Epub 2013 Apr 29. PubMed PMID: 23630210.
4: Fong CY, Grigoriadis G, Hocking J, Coutsouvelis J, Muirhead J, Campbell P, Paul E, Walker P, Avery S, Patil S, Spencer A, Schwarer A, Wei A. Fludarabine, cytarabine, granulocyte-colony stimulating factor and amsacrine: an effective salvage therapy option for acute myeloid leukemia at first relapse. Leuk Lymphoma. 2013 Feb;54(2):336-41. doi: 10.3109/10428194.2012.713479. Epub 2012 Sep 8. PubMed PMID: 22812445.
5: Jangir DK, Dey SK, Kundu S, Mehrotra R. Assessment of amsacrine binding with DNA using UV-visible, circular dichroism and Raman spectroscopic techniques. J Photochem Photobiol B. 2012 Sep 3;114:38-43. doi: 10.1016/j.jphotobiol.2012.05.005. Epub 2012 May 18. PubMed PMID: 22677564.
6: Ketron AC, Denny WA, Graves DE, Osheroff N. Amsacrine as a topoisomerase II poison: importance of drug-DNA interactions. Biochemistry. 2012 Feb 28;51(8):1730-9. doi: 10.1021/bi201159b. Epub 2012 Feb 10. PubMed PMID: 22304499; PubMed Central PMCID: PMC3289736.
7: Attia SM. Molecular cytogenetic evaluation of the mechanism of genotoxic potential of amsacrine and nocodazole in mouse bone marrow cells. J Appl Toxicol. 2013 Jun;33(6):426-33. doi: 10.1002/jat.1753. Epub 2011 Nov 11. PubMed PMID: 22081495.
8: Devi ML, Chandrasekhar KB, Surendranath KV, Rao BM, Narayana MB. A validated stability-indicating RP-HPLC assay method for Amsacrine and its related substances. J Chromatogr Sci. 2011 Aug;49(7):489-94. PubMed PMID: 21801478.
9: Wilhelm C, Neubauer A, Burchert A. Poor-risk cytogenetics may be associated with inferior outcome after fludarabine, cytarabine, and amsacrine reduced intensity conditioning in patients with high-risk acute myeloid leukemia. Leuk Lymphoma. 2011 Oct;52(10):2031-5. doi: 10.3109/10428194.2011.588760. Epub 2011 Jun 24. PubMed PMID: 21702642.
10: Zhang L, Guo Y, Wang J, Wang X, Han G, Ou W, Xu Y, Zhang X. Assisted sonodynamic damage of bovine serum albumin by metronidazole under ultrasonic irradiation combined with photosensitive antitumor drug-Amsacrine. J Photochem Photobiol B. 2010 Jan 21;98(1):61-8. doi: 10.1016/j.jphotobiol.2009.11.005. Epub 2009 Nov 22. PubMed PMID: 20006932.
| Chemical | |
|---|---|
| CAS Num | 51264-14-3 (Amsacrine) |
| Chemical Formula | C21H20ClN3O3S |
| Molecular Weight | 429.92 |
| IUPAC Chemical Name | N-(4-(acridin-9-ylamino)-3-methoxyphenyl)methanesulfonamide hydrochloride |
| Elemental Analysis | C, 58.67; H, 4.69; Cl, 8.25; N, 9.77; O, 11.16; S, 7.46 |
| Synonym | acridinyl anisidide; Cains Acridine. US brand name |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | CS(=O)(NC1=CC=C(NC2=C(C=CC=C3)C3=NC4=CC=CC=C42)C(OC)=C1)=O.[H]Cl |
| Biological | |
| Targets and Effects | topoisomerase II |
| Pathways | Apoptosis |
| Physical | |
| Appearance | white solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >2 years if stored properly |
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